DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
This office action is a response to applicant’s communication submitted April 4, 2024.
Claims 1-35 are pending in this application.
Priority
This application is a continuation in part of PCT/US2022/045177 filed 09/29/2022 and claims benefit to US provisional application 63/253,307 filed 10/07/2021.
Claim Objections
Claims 3-4, 10-11, 13, 18-19, and 25-26 are objected to because of the following informalities:
Claims 3 and 18 the phrase “is an acidic ionic liquid, a Bronsted acidic ionic liquid” should read “is an acidic ionic liquid or a Bronsted acidic ionic liquid” to differentiate them as alternatives.
Claims 4 and 19 recite the phrase “Bronsted”, but in other instances the term utilizes an umlaut for the “o”.
In claims 10-11 and 25-26: The phrase “hepyl” should read “heptyl”.
In claims 10 and 25 the phrase “wherein the ionic liquid is a halogen substituted 1-hepyl-3-methlimidazolium halide” should read “wherein the ionic liquid is selected from” to avoid redundancy and confusion.
In claim 13, “IL” should be defined.
In claims 10 and 26 the phrase “wherein the ionic liquid comprise an acetate salt as the anion is selected from” should read “wherein the ionic liquid is selected from” to avoid redundancy and confusion.
Appropriate correction is required.
Specification
The disclosure is objected to because of the following informalities:
On page 1 of the instant specification, the phrase “flexible electronics79°” should read “flexible electronics79” (para. 0004).
On page 6 of the instant specification entry 8 of the table recites the phrase “Error! Bookmark not defined.q”, which should be deleted.
On page 14 of the instant specification, para. 0059 refers to figure 8 as showing a powder x-ray diffraction image, however figure 8 appears to be a transmission electron microscopy image.
On page 14 of the instant specification, para. 0062 refers to figure 11 as showing a transmission electron microscopy image, however figure 11 appears to be an FTIR spectrum.
On page 15 of the instant specification, para. 0064 refers to a figure 13, however only 12 figures are provided.
Appropriate correction is required.
Drawings
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they do not include the following reference sign(s) mentioned in the description: According to the instant specification, there is a 13th figure (pg. 15, para. 0064), however it is not included in the drawing. Additionally see issues with specification described above, wherein the details described in the specification do not match up with the attached figures. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Interpretation
Claims 33-35 are product by process claims. The Examiner notes that, "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process" In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (See MPEP 2113 (I)).
Claim Rejections - 35 USC § 112 (b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-35 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claims 1-35: The terms “high” or “highly” in claims 1, 13, 15, 17, 28, 30, and 33 are relative terms which renders the claim indefinite. The terms “high” or “highly” are not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. It is unclear what constitutes a “high” aspect ratio, crystalline, thermal stability, modulus, stiffness, strength, binding energy. Claims 2-16 which depend from claim 1 are similarly rejected. Claims 18-32 which depend from claim 17 are similarly rejected. Claims 34-35 which depend from claim 33 are similarly rejected.
Regarding claims 1-32: Claim 1 recites inter alia, “A method for the preparation of chitin nanocrystals, nanowhiskers, or both…” and “comprising: isolating chitosan nanocrystals and nanowhiskers”. Claim 17 recites inter alia, “A method for the preparation of chitin nanocrystals, nanowhiskers, or both…”, “comprising: isolating in a single step a purified chitin nanowhiskers”, and “wherein the chitin nanocrystals and nanowhiskers comprise….”. The claims are unclear because the method suggests preparation of nanocrystals, nanowhiskers in the alternative, but the method steps describe a process of isolating nanocrystals and nanowhiskers (i.e. both) as recited by instant claim 1 or solely isolating nanowhiskers (single), and then referencing both chitin nanocrystals and nanowhiskers (both) as recited by instant claim 17. Thus the lack of clarity renders claims 1 and 17 indefinite as a person of ordinary skill in the art would be unable to ascertain the metes and bounds of the invention. Claims 2-16 which depend from claim 1 are similarly rejected. Claims 18-32 which depend from claim 17 are similarly rejected.
Regarding claims 4 and 19: Claims 4 recite the limitation "the ionic liquid cation”. There is insufficient antecedent basis for this limitation in the claim.
Regarding claims 4 and 19: Claim 4 recite the phrase “Bronsted-acidic anion (acidic IL). However the use of “acidic IL” leads to confusion as “acidic IL” is not synonymous with “Bronsted-acidic anion”, which is a specific acidic anion. It is unclear whether the remainder of the claim is limiting to bronsted-acidic anions only, or acidic ionic liquids generally. Thus, claims 4 and 19 are rendered indefinite for a lack of clarity.
Regarding claims 4 and 19: The use of parenthesis for definitions of R groups as in,
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renders the claim indefinite as it is unclear whether the phrases in parenthesis are merely exemplary or required limitions to the claim. The lack of clarity renders the claims indefinite.
Regarding claims 5 and 20: Claims 5 and 20 recites “wherein the cation is selected from”, but includes ionic liquids with both anions and cations. It is unclear whether the claims are specific to only cation portions of the ionic liquids or the whole ionic liquid, which conflicts with the claim limitation of cations.
Regarding claims 5 and 20: The provided structures possess R groups which are not defined, thus a person of ordinary skill in the art would be unable to ascertain the metes and bounds of the invention. Additionally the structures are recited in such a way that is unclear that they are tied to the aforementioned compound, “
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”. In other words are the phrases imidazolium or substituted imidazolium meant to be limited to these specific structures, or are they presented in an addition to the broader imidazolium or substituted imidazolium words.
Regarding claims 9 and 24: Claims 9 and 24 recite “wherein the ionic liquid is selected from at least one of: 1-methylimiadazolim, 1-ethylimidazolium….”. However the species recited are not ionic liquids, but cations that may be in an ionic liquid. The lack of clarity renders the claims indefinite.
Claims 12, 27-28, 30-32 recites the limitation "the purified chitin". There is insufficient antecedent basis for this limitation in the claim. Additionally, it is unclear whether the phrase is in reference to pure chitin obtainable by the chitin biomass, or is in reference to the chitin nanocrystals or nanowhiskers.
Regarding claim 13: Claim 13 recites, “wherein a product from a treatment of crustacean biomass with IL.” It is unclear whether the phrase is directed towards a specific embodiment of the base method, or some other process. The lack of clarity renders the claim indefinite.
Regarding claims 13 and 28: The phrase in parenthesis in the phrase “a high aspect ratio (10-100)” renders the claim indefinite because it is exemplary of a high aspect ratio, or is meant to limit the aspect ratio to specifically this range.
Regarding claim 15 and 30: The phrase in parenthesis in the phrase “a high modulus (200 GPa)” renders the claim indefinite because it is exemplary of a high modulus, or is meant to limit the modulus to specifically this value.
Claims 16 recites the limitation "the crustacean biomass". There is insufficient antecedent basis for this limitation in the claim.
Regarding claim 29: Claim 29 recites “wherein a yield of chitin from the raw chitinous biomass is at least 40, 50, 60, or 70 %”. It is unclear whether the yield of chitin is in reference to total chitin obtained from the biomass, or is in reference to the chitosan nanocrystals and nanowhiskers, similar to claim 14.
Regarding claims 33-35: Claim 33 is drawn to “a purified chitin nanocrystal”, and recites the phrase “purified chitin”, but it is unclear whether terms “purified chitin nanocrystal” and “purified chitin” are to be interpreted interchangeably, or wherein “extracting a purified chitin” is a step that eventually leads to a purified chitin nanocrystal. Claims 34-35 which depend from claim 33 are similarly rejected.
Regarding claims 33-35: Claim 33 recite the limitation "the chitin…. nanowhiskers". There is insufficient antecedent basis for this limitation in the claim. Claims 34-35 which depend from claim 33 are similarly rejected.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 33-35 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kadokawa (Carbohydrate Polymers, 2011, IDS filed October 24, 2024).
Regarding claims 33-35: Kadokawa teaches the preparation of chitin nanowhiskers using an ionic liquid, 1-allyl-3-methylimidazolium bromide (AMIMBr) (abstract). Kadokawa teaches the chitin is sourced from crab shells (pg. 1409, col. 1, para. 2). Kadokawa teaches the nanowhiskers were crystalline (pg. 1410, col. 1, para. 2). As discussed above in the claim interpretation section above, that, "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. Thus, although Kadokawa teaches formation from a pure chitin polymer (not from raw biomass), wherein Kadokawa teaches the preparation of chitosan nanowhiskers from crab chitin using an ionic liquid, the chitosan nanocrystal is identical to the chitosan nanocrystal as recited by instant claims 33-35, absent evidence to the contrary.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1-2, 5, 7, 12-17, 20, 22, 27-32 are rejected under 35 U.S.C. 103 as being unpatentable over Kadokawa (Carbohydrate Polymers, 2011, IDS filed October 24, 2024) as applied to claims 33-35 above in view of Setoguchi (International Journal of Biological Macromolecules, 2012, cited on PTO-892) as evidenced by Qin (Green Chem., 2010, cited on PTO-892).
Regarding claims 1-2, 5, 7, 12, 15-17, 20, 22, 27-28, 30-32: Kadokawa teaches the preparation of chitin nanowhiskers using an ionic liquid, 1-allyl-3-methylimidazolium bromide (AMIMBr) (abstract). Kadokawa teaches the chitin is sourced from crab shells (pg. 1409, col. 1, para. 2). Kadokawa teaches the nanowhiskers were crystalline (pg. 1410, col. 1, para. 2). Kadokawa teaches chitin was swollen with AMIMBr by soaking at room temperature, followed by heating at 100 C, soaking the resulting gel in methanol and subsequent sonication gave a chitin dispersion, and the SEM image of the dispersion showed the formation of chitin nanowhiskers (abstract).
Kadokawa does not teach wherein the chitin nanocrystals a prepared directly from raw chitinous biomass without prior isolation of a raw chitin polymer. Kadokawa teaches the preparation of chitin nanocrystals from chitin powder isolated from crab shells.
However, Setoguchi teaches facile production of chitin from crab shells was performed by direct extraction using an ionic liquid, 1-allyl-3-methylimidazolium bromide (AMIMBr) (abstract).
Taken together it would have been prima facie obvious to a person of ordinary skill in the art to modify the method of Kadokawa such that the chitin is produced directly from crab shells as taught by Setoguchi. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success in order to streamline the process of preparing chitin nanowhiskers and the art demonstrates AMIMBr can product chitin from crab shells and also convert chitin to chitin naowhiskers.
Regarding claim 13: Kadokawa teaches the chitin nanowhiskers with ca. 20–60nm in width and several hundred nanometers in length (pg. 1411, col. 2, para. 2). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists (See MPEP 2144.05 (I)).
Regarding claims 14 and 29: Although Kadokawa does not explicitly state measuring yield of the nanowhiskers, Qin discloses that ionic liquids recover 94% chitin from shrimp shells which could be spun directly from the solution in a one-pot process (pg. 970, table 2, col. 1, para. 3). Thus, wherein Kadokawa teaches conversion of chitin into chitin nanowhiskers, and it would be obvious to isolate chitin from chitaneous material, the yields are expected to be within the claimed range and are a result of practicing the method rendered obvious, absent evidence to the contrary.
Claims 3-4, 8, 18-19, and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Kadokawa (Carbohydrate Polymers, 2011, IDS filed October 24, 2024), Setoguchi (International Journal of Biological Macromolecules, 2012, cited on PTO-892), Qin (Green Chem., 2010, cited on PTO-892) as applied to claims 1-2, 5, 7, 12-18, 20, 22, 27-35 above in view of Silva (Green Chem., 2017, cited on PTO-892).
Regarding claims 3-4, 8, 18-19, and 23: As discussed above the prior art renders obvious the methods of claims 1 and 17.
They do not teach wherein the ionic liquid is a Bronsted-acidic anion acidic IL, such as dimethylphosphate, or a 1-ethyl-3-methylimidazolium salt.
However, Silva teaches Ionic liquids (ILs) have huge potential to provide advances in many areas such as energy, pharmaceutical formulations, biomedical sciences, and technology. In the biomedical field, ILs have been intensively investigated for use as potential solvents for some polysaccharides to overcome their lack of solubility and processability (abstract). Dissolution of chitin and chitosan in ILs such as 1-butyl-imidazolium acetate (BMIMAc) and 1-ethyl-3-methylimidazolium chloride (BMIMCl) has been used to create materials including sponges, films, microspheres, and aerogels. Moreover, ILs have a key role in chemical reactions, hydrolysis, acetylation, deacetylation and graft copolymerization of chitin/chitosan, promoting homogeneous media and thus enhancing the efficiency of the reactions (abstract). Silva teaches ILs could be used as non-derivatizing solvents for native cellulose (pg. 1209, col. 1, para. 2. The success of dissolving cellulose in ILs has initiated a series of studies on the dissolution of other biopolymers (pg. 1209, col. 1, para. 2. Particularly for chitin/chitosan, ILs have been employed not only as solvents but also as reaction media to modify them, and to promote the production of 2D- and 3D-based chitin and chitosan matrices (micro/nanoparticles, gels, films, sponges) (pg. 1209, col. 1, para. 2). Silva teaches Many ILs have been reported in the literature with the ability to dissolve chitin and chitosan, for example, 1-allyl-3-methylimidazolium bromide (AMIMBr), 1-allyl-3-methylimidazolium chloride (AMIMCl), 1-ethyl- 3-methylimidazolium chloride (EMIMCl), 1-butyl-3-methylimidazolium chloride (BMIMCl), 1-allyl-3-methylimidazolium bromide (AMIMBr), 1-butyl-3-methylimidazolium acetate (BMIMAc), 1-ethyl-3-methylimidazolium acetate (EMIMAc), 1-ethyl-3-methylimidazolium dimethyl phosphate ([EMIM][Me2PO4]), and 1-carboxymethyl-3-methylimidazolium hydrochloride ([IMIM-COOH]Cl) (pg. 1209, col. 2, para. 2).
Taken together it would have been prima facie obvious to substitute AMIMBr with either 1-ethyl-3-methylimidazolium acetate (EMIMAc) or 1-ethyl-3-methylimidazolium dimethyl phosphate ([EMIM][Me2PO4]) as suggested by Silva. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success as these ionic liquids are all capable of dissolving chitin, and it is prima facie obvious to substitute equivalents known for the same purpose (See MPEP 2144.06 (II)).
Claims 6, 9-11, 21, and 24-26 are rejected under 35 U.S.C. 103 as being unpatentable over Kadokawa (Carbohydrate Polymers, 2011, IDS filed October 24, 2024), Setoguchi (International Journal of Biological Macromolecules, 2012, cited on PTO-892), Qin (Green Chem., 2010, cited on PTO-892), and Silva (Green Chem., 2017, cited on PTO-892) as applied to claims 1-5, 7-8, 12-20, 22-23, and 27-35 above in view of Brandt (US 20140073016, IDS filed October 24, 2024).
Regarding claims 6, 9-11, 21, and 24-26: As discussed above the prior art renders obvious the methods of claims 1 and 17. Silva teaches the ionic liquid (IL) platform can also be used to change our perspective on the challenge of isolation and processing of components from lignocellulosic biomass and also chitin from crab shells (pg. 1210, col. 1, para. 3).
They do not teach wherein the ionic liquid is 1-ethyl-3-methylimidazolium hydrogen sulfate, the cation is 1-butylimidazolium halide, or wherein the ionic liquid is 1-heptyl-3-methylimidazolium acetate.
However, Brandt teaches solubilizing lignin in lignocellulosic biomass using ionic liquids (pg. 2,para. 0019). The combination of anions and cations can be chosen to match the particular application required (pg. 1, para. 0004). Brandt teaches the term "ionic liquid" refers to an ionized species (i.e. cations and anions) (pg. 2, para. 0018). Preferably the anion is selected from methy 1 sulfate [MeSO4]-, hydrogen sulfate [HSO4]-, methanesulfonate [MeSO3]-, and acetate [MeCO2] (pg. 2, para. 0018). Brandt teaches the cation is preferably selected from imidazolium or pyridinium (pgs. 2-3, para. 0031). Brandt teaches preferred ionic liquids for use in the invention are l-butyl-3-methylimidazolium methyl sulfate [C4C1im] [MeSO4 ], l-butyl-3-methylimidazolium hydrogen sulfate [C4C1im][HSO4 ], l-butyl-3-methylimidazolium methanesulfonate [C4C1im][MeSO3], 1-butylimidazolium hydrogen sulfate [C4Him][HSO4 ], and l-ethyl-3-methylimidazolium acetate [C2C1im][MeCO2] (pg. 3, para. 0035). Brandt teaches that alkyl group moieties can contain 2-10 carbon atoms (pg. 3, para. 0033). Brandt demonstrates that interchanging anions, including hydrogen sulfate, as well as adjusting length of alkyl groups on imidazolium cations (i.e.ethyl, butyl, methyl) is a known technique in the art.
Taken together it would have been prima facie obvious to substitute AMIMBr with either 1-ethyl-3-methylimidazolium hydrogen sulfate, the cation is 1-butylimidazolium halide, or wherein the ionic liquid is 1-heptyl-3-methylimidazolium acetate as suggested by Brandt. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success as the art recognizes the ability of ionic liquids to dissolve biomass generally, and it is prima facie obvious to substitute equivalents known for the same purpose (See MPEP 2144.06 (II)). Additionally, substituting known cations/anions for one another is a routine practice in the art of ionic liquids for treating biomass compositions and would be within the technical grasp of the skilled invention. Wherein the art recognizes the applicability of ionic liquids in dissolving both lignocellulosic and chitinous biomass, known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art (See MPEP 2143 (IF)). Compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties (See MPEP 2144.09 (II)). Thus, a person of ordinary skill in the art would have the modification to include heptyl alkyl groups by modifying the chain length of imidazolium alkyl groups and arrive at 1-heptyl-3-methylimidazolium acetate as claimed.
Conclusion
No claims are allowed in this action.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Chowdhury (BioResources, 2014, cited on PTO-892) teaches the use of ionic liquids to dissolve biomass (abstract).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAMUEL L GALSTER whose telephone number is (571)270-0933. The examiner can normally be reached Monday - Friday 8:00 AM - 5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SAMUEL L GALSTER/Examiner, Art Unit 1693
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